4-(Bromoacetyl)benzonitrile → 4-[2-(2-Imino-4,4-dimethyl-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl]benzonitrile

HRID 1436391Notes

Reaction equation

HRID 1436391 reaction equation
[OH:1][CH2:2][C:3]([NH:6][C:7]1[S:8][CH:9]=[C:10]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)[N:11]=1)([CH3:5])[CH3:4].BrCC(C1C=CC([C:28]#[N:29])=CC=1)=O.C1N=CN(C(N2C=NC=C2)=N)C=1>O1CCCC1>[NH:29]=[C:28]1[N:6]([C:7]2[S:8][CH:9]=[C:10]([C:12]3[CH:13]=[CH:14][C:15]([C:16]#[N:17])=[CH:18][CH:19]=3)[N:11]=2)[C:3]([CH3:5])([CH3:4])[CH2:2][O:1]1

Participants

5

Reactant 3

HCID 986544-(Bromoacetyl)benzonitrileHCID 113556541-(1H-imidazole-1-carboximidoyl)-1H-imidazoleHCID 866185984-{2-[(2-Hydroxy-1,1-dimethylethyl)amino]-1,3-thiazol-4-yl}benzonitrile

Product 1

HCID 247845394-[2-(2-Imino-4,4-dimethyl-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl]benzonitrileYield 19%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-{2-[(2-hydroxy-1,1-dimethylethyl)amino]-1,3-thiazol-4-yl}benzonitrile (2.00 g, 7.31 mmol), prepared in the same manner as described in step 3 of Example 52, and replacing 3-(2-bromoacetyl)benzonitrile with 4-(2-bromoacetyl)benzonitrile, and C-(di-imidazol-1-yl)-methyleneamine (1.30 g, 8.07 mmol) in 35 mL of tetrahydrofuran was refluxed under nitrogen for three days. The reaction was concentrated under reduced pressure to remove the tetrahydrofuran. The residue was partitioned between methylene chloride and water. The organic layer was separated, dried (MgSO4), filtered and the solvent removed under reduced pressure. Purification of the residue on a Horizon™ Flash Collector (the Biotage FLASH 40+™ cartridge) using a linear gradient of hexane in methylene chloride as the eluent gave the title compound (417.2 mg, 19%) as an off-white solid, mp 158-161° C.; MS (ES) m/z 299.0 [M+H]+. Anal. Calcd for C15H14N4OS: C, 60.38; H, 4.73; N, 18.78. Found: C, 60.38; H, 4.82; N, 18.67.

Workup

  1. customprepared in the same manner
  2. temperaturewas refluxed under nitrogen for three days
  3. concentrationThe reaction was concentrated under reduced pressure
  4. customto remove the tetrahydrofuran
  5. customThe residue was partitioned between methylene chloride and water
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent removed under reduced pressure
  10. customPurification of the residue on a Horizon™ Flash Collector (the Biotage FLASH 40+™ cartridge)

Sources & evidence

ORD record
ord-da29f274a8b44f7f9132d07b663820a9
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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